n-Dodecyl-(p-methylphenyl)-keton | 94760-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: n-Dodecyl-(p-methylphenyl)-keton
• 英文别名: 1-(4-Methylphenyl)tridecan-1-one
• CAS: 94760-85-7
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: MSVNPEMNSPIGCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  n-Dodecyl-(p-methylphenyl)-keton 在 sodium tetrahydroborate 、 Burkholderica cepacia amano lipase 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 0.5h， 生成 (R)-1-(p-methylphenyl)-1-tridecanol
  参考文献：
  名称：

  Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution

  摘要：

  The present study deals with the biocatalytic enantioselective synthesis of 19 new chiral alcohols with alkyl (C-11-C-19) and phenyl, substituted phenyl, heteroaromatic, and naphthyl groups 4a-4z with an (R)-configuration and high enantiomeric excess (similar to 100%). The corresponding ketones 1a-1z were synthesized and then reduced with NaBH4 to their racemic alcohols 2a-2z, which were converted into their racemic acetyl derivatives 3a-3z. Enzymes of four different types were used for the enantioselective hydrolysis of these acetyl compounds 3a-3z. The optimal reaction conditions for these four enzymes were established by investigating the enantiomeric excesses by chiral HPLC. Amano lipase from Burkholderica cepacia (Pseudomonas cepacia) AL-PS was determined as the best enzyme in this work This study presents an environmentally friendly and green chemistry method for the synthesis of these new (R)-chiral carbinols 4a-4z. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.017
• 作为产物：
  描述：

  月桂酸 在 4-二甲氨基吡啶 、 iron(III) trifluoromethanesulfonate 、 三氟甲磺酸 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.67h， 生成 n-Dodecyl-(p-methylphenyl)-keton
  参考文献：
  名称：

  末端炔烃与烷基过氧化物的铁催化自由基脱羧氧化烷基化

  摘要：

  已经研究了以烷基过氧化物作为烷基化试剂的炔烃的铁催化的烷氧基化反应。烷基过氧化物可容易地从脂族酸获得，并且同时用作烷基化试剂和内部氧化剂。脂肪酸的伯，仲和叔烷基易于掺入C-C三键中，并合成了多种α-烷基化的酮。机理研究表明，该反应涉及高反应性烷基自由基。观察到铁（III）催化剂催化的月桂酸和水之间的独特平衡。

  DOI：

  10.1002/chem.201701830

文献信息

• Synthesis of New Chiral and Racemic 1,3-Dioxolanes
  作者：Hatice Başpınar Küçük、Ayşe Yusufoğlu

  DOI：10.1002/jhet.937

  日期：2012.9

  A series of chiral 1,3‐dioxolanes, 3–12, with >99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C11—AC13). Their ee values were determined by chiral high‐performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3‐dioxolanes rac‐3–12, which were also

  合成了一系列手性1,3-二氧戊环3 – 12，ee值> 99％。这是从酮与芳基，单取代的芳基和长烷基链（C 11 -AC 13）开始的手性缩酮化反应的首次研究。其EE值通过在Chiralcel OD柱上的手性高效液相色谱法（HPLC）测定，使用它们的外消旋的1,3-二恶戊环外消旋3 - 12，这也被合成为第一次。这些手性和外消旋的1,3-二氧戊环酮通过红外，NMR（1 H，13 C），质谱，元素分析，旋光和手性HPLC进行表征。
• Energy-Transfer-Enabled Radical Acylation Using Free Alkyl Boronic Acids through Photo and NHC Dual Catalysis
  作者：Wan-Cong Liu、Xiang Zhang、Lin Chen、Rong Zeng、Yuan-Hang Tian、En-Dian Ma、Ya-Peng Wang、Bin Zhang、Jun-Long Li

  DOI：10.1021/acscatal.3c06027

  日期：2024.3.1

  for ketone synthesis. As an important coupling partner, bench-stable and commercially available alkyl boronic acids are widely used in transition metal catalysis, but they are rarely utilized as radical precursors for acylative coupling reactions. Herein, we reported an energy-transfer-enabled radical acylation using free alkyl boronic acids via NHC/photo dual catalysis. This protocol could efficiently

  交叉偶联反应作为最流行的酮合成方案之一而广受好评。作为重要的偶联伙伴，实验室稳定且市售的烷基硼酸广泛用于过渡金属催化，但很少用作酰化偶联反应的自由基前体。在此，我们报道了通过 NHC/光双催化使用游离烷基硼酸实现能量转移的自由基酰化。该方案可以有效促进烷基硼酸与酰基咪唑之间的铃木型交叉偶联以及烯烃的多组分烷基酰化，从而产生具有结构多样性的各种酮。此外，酮产品可以很容易地转化为大量结构有趣的精细化学品。初步机理研究揭示了独特的自由基反应机理。
• Asinger,F. et al., Journal fur praktische Chemie (Leipzig 1954), 1963, vol. 22, p. 153 - 172
  作者：Asinger,F. et al.

  DOI：——

  日期：——
• Asymmetric synthesis of new chiral long chain alcohols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2010.12.010

  日期：2010.12

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of new chiral 1,2- and 1,3-diols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1007/s00706-012-0792-7

  日期：2013.2

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.